5-Benzoyl-2-(1H-indol-3-yl)-4-(4-methyl­phen­yl)-4,5-dihydro­furan-3-carbonitrile

J Suresh; R Vishnupriya; P Gunasekaran; S Perumal; P L Nilantha Lakshman

doi:10.1107/S1600536812011105

. 2012 Mar 21;68(Pt 4):o1124. doi: 10.1107/S1600536812011105

5-Benzoyl-2-(1H-indol-3-yl)-4-(4-methylphenyl)-4,5-dihydrofuran-3-carbonitrile

J Suresh ^a, R Vishnupriya ^a, P Gunasekaran ^b, S Perumal ^b, P L Nilantha Lakshman ^c,^*

PMCID: PMC3344070 PMID: 22589979

Abstract

The furan ring in the title compound, C₂₇H₂₀N₂O₂, adopts a twisted conformation about the sp ³—sp ³ bond. The molecular structure is stabilized by an intramolecular C—H⋯O interaction which generates an S(6) ring motif. The crystal packing is stabilized by N—H⋯O and C—H⋯O interactions generating centrosymmetric R ₂ ²(18) and C(6) chain motifs, respectively. A weak C—H⋯π interaction is also observed.

Related literature

For the biological importance of furan derivatives, see: Auvin & Chabrier De Lassauniere (2005 ▶). For hydrogen-bonding graph-set notation, see: Bernstein et al. (1995 ▶). For additional conformation analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₂₇H₂₀N₂O₂
M _r = 404.45
Monoclinic,
a = 9.8084 (4) Å
b = 15.9553 (7) Å
c = 13.8782 (7) Å
β = 107.185 (2)°
V = 2074.92 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.19 × 0.15 × 0.12 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.967, T _max = 0.974
21144 measured reflections
4647 independent reflections
3017 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.133
S = 1.02
4647 reflections
284 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812011105/tk5068sup1.cif

e-68-o1124-sup1.cif^{(22.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011105/tk5068Isup2.hkl

e-68-o1124-Isup2.hkl^{(227.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812011105/tk5068Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C51–C56 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C33—H33⋯O1	0.93	2.52	3.032 (2)	115
N2—H2⋯O2ⁱ	0.91 (2)	2.04 (2)	2.880 (2)	154
C44—H44⋯O2ⁱⁱ	0.93	2.55	3.329 (3)	142
C34—H34⋯Cg1ⁱⁱⁱ	0.93	2.69	3.556 (3)	156

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

JS thanks the UGC for the FIST support. JS and RV thank the management of Madura College for their encouragement and support. PG thanks the CSIR for a Junior and Senior Research Fellowship. SP thanks the Department of Science and Technology, New Delhi, for funding the Indo-Spanish collaborative major research project (grant No. DST/INT/SPAIN/09).

supplementary crystallographic information

Comment

Furanyl derivatives have calplain-inhibiting activity and are used in the preparation of medicaments for the treatment of inflammatory and immunological diseases, cardiovascular and cerebro-vascular diseases, disorders of the central or peripheral nervous system, cachexia, osteoporosis, muscular dystrophy, proliferative diseases, cataracts, rejection reactions following organ transplants and auto-immune and viral diseases (Auvin et al., 2005). The high medicinal value of these compounds in conjunction with our research interests prompted us to synthesize and report the X-ray structure of the title compound.

In the title compound (Fig 1), the five-membered furanyl ring adopts a twisted conformation as evident from the puckering parameters (Cremer & Pople, 1975) Q = 0.192 (2) Å and φ = 129.0 (6)°. The five-(N2/C38/C31/C32/C37) and six-membered (C32—C37) rings in the indole group are planar, with a dihedral angle of 0.74 (1)° between them. The dihedral angle between the phenyl rings (C42—C47 and C51—C56) is 15.24 (1)°.

Fig. 2 shows the partial packing of molecules in the crystal structure. The C—H···O and N—H···O intermolecular interactions generate C₁¹(6) chain and centrosymmetric R₂²(18) motifs, respectively (Bernstein et al., 1995). In addition, there is a weak C—H···π interaction, viz, C34—H34···Cg1ⁱⁱ_,Table 1.

Experimental

To a stirred mixture of 2-(1H-indole-3-carbonyl)-3-p-tolylacrylonitrile (1.0 molar eq.) and phenacylpyridinium bromide (1.0 molar eq.) in water (10 ml) was added drop wise triethylamine (0.25 molar eq.) at room temperature. The resulting clear solution, that slowly became turbid, was stirred at room temperature for 1 h. Then, the separated free flowing solid was filtered and washed with methanol (3 ml) to afford the title compound as a pale-yellow solid. The product thus obtained was recrystallized from an EtOH-EtOAc mixture (1:1 ratio v/v ml) to the give pure compound as pale-yellow crystals. Yield: 92%. M.pt: 502 K.